


Littlered and Alpha5

by Triangulum



Category: Teen Wolf (TV)
Genre: Alternate Universe - Human, Anal Fingering, Anal Sex, Camboy Stiles Stilinski, College Student Stiles, Humiliation, Loss of Virginity, M/M, Masturbation, Sex Toys, Small Dick Stiles
Language: English
Status: Completed
Published: 2017-08-04
Updated: 2017-08-04
Packaged: 2018-12-09 15:51:48
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 9,372
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11672262
Author URL: https://archiveofourown.org/users/Triangulum/pseuds/Triangulum
Summary: Stiles could say that he's a grower not a shower, but that would be a lie. On a good day, fully erect, he's three inches long. Okay, two-and-a-half. Whatever, it works for him. It's what got him into camming in the first place. There's a very specific clientele out there that's looking for exactly what Stiles has. The lithe, gay guy with a small dick is a very niche market and Stiles has managed to carve out his own place in it. The fact that he's a virgin only helps.OrStiles is a camboy and Peter is his best client.





	Littlered and Alpha5

**Author's Note:**

  * For [WithMyTeeth (Ylith)](https://archiveofourown.org/users/Ylith/gifts).



> This is for WithMyTeeth for the Summer of Discord exchange! I hope you enjoy, lovely!

Stiles could say that he's a grower not a shower, but that would be a lie. On a good day, fully erect, he's three inches long. Okay, two-and-a-half. Whatever, it works for him. It's what got him into camming in the first place. There's a very specific clientele out there that's looking for exactly what Stiles has. The lithe, gay guy with a small dick is a very niche market and Stiles has managed to carve out his own place in it. The fact that he's a virgin only helps. 

It was Erica that had first turned Stiles on to being a camboy. She does some camming occasionally for extra money and had told Stiles he might as well try. His scholarship covers a lot, but not enough for basic survival, and he hates his dad having to give him so much money. If he plays his cards right, he can make more in one cam session than he does for a whole week at his part-time job. 

Erica set him up with an account on the same website she uses ("Why'd you call me littlered?" "You always are wearing a red sweatshirt." "SO?!" "And you know...it's little.") and gave him a few tips before she set him free into the camboy wild. He'd been nervous at first. He's not exactly well-endowed, would people even want to see him? But then the subscribers started pouring in. He started out by just stripping, then added in some panties to the mix, before progressing into masturbating on camera. He does live shows, then puts the the videos up to buy. In the first month, he made nearly enough to cover his rent. There's a niche market, and Stiles had tapped into it.

Stiles doesn't do it because he has to, though. He does it because he loves it. He could stop right now and be set for rent for the next three months. He likes being watched, he likes knowing that all those people out there desire him. He even likes some of their comments. There are some that are unnecessary or just rude, but there are some that he loves. Some are suggestions or requests for content and sometimes Stiles even listens. 

Alpha5 is probably his favorite customer. He pays for all Stiles' videos and almost never misses a live show. He's also the one subscriber that hasn't whined about wanting free content. To be honest, it's his comments that usually spur Stiles on. Sometimes he'll read them while he plays with himself on camera. There's a live group chat set up on the website so the viewers can connect with him. Sometimes Alpha5 is quiet, sometimes he tells Stiles how beautiful his little cock is, how wonderful it looks disappearing into Stiles' fist. Stiles always blushes bright red, his dick twitching in desire. 

Tonight, Stiles is doing something different. He's stripped on camera before and played with his little cock, but never played with his ass. Stiles sets up his laptop as usual, aiming the webcam at his bed. As soon as it hits 9:00 pm, Stiles starts the live feed. The group chat explodes with hellos and other comments. 

"Hey all," Stiles says, waving at the camera. As usual, he's wearing a t-shirt and jeans. He'd started out just stripping before things got dirtier and dirtier. Now, he regularly masturbates on camera, but he still does the stripping portion of his show. It brought everyone in and they seem to enjoy it.

"We're going to try something a little different tonight. I hope you all like it," Stiles says. He glances down at the chat and sees some apprehension, but most of his viewers seems excited and cheer him on.

Stiles grins and starts slowly pulling off his clothes, revealing his skin inch by inch. Soon enough, his shirt is dropping to the floor, followed by his jeans, leaving him in nothing but a jock strap. He kneels on the bed, exposing his ass to the camera. He runs his hands over his skin, spreading himself wide to show off his tight hole. He looks over his shoulder at the camera and runs a dry finger over his hole. He can see the chat blowing up, but he can't read anything from here. He has a good idea of what it says, though.

He turns back and slowly pulls the jock strap down, freeing his hard little cock. He spreads his legs wide for the camera, cupping his tiny cock and balls to show off his hole. Reaching under the pillow, he retrieves the bottle of lube he'd stashed there earlier. He pours a little bit on his fingers, warming it up a bit before reaching between his legs.

The lube is still a little cold and Stiles hisses at the first contact. He rubs his finger around his rim, coaxing it to relax before slowly sliding a finger into himself. Stiles moans and throws his head back. He's acting a bit, he plays with himself enough that one finger isn't really that big of a deal, but part of his appeal is that he's a small-cocked virgin, so his viewers like to see him act like everything is new and exciting.

Stiles slowly adds a second finger, working them in and out of his greedy hole, before adding a third. Stiles' moans are real now as he stretches the capacity of his ass. He usually fingers himself with two fingers, playing with his prostate, and he rarely goes to three. He mewls as his fingers press against his prostate, making his cock jerk and spurt out precum. 

"Fuck," Stiles groans. 

Stiles uses his free hand to stroke over his cock in short, quick jerks. He's close already, whining and gasping. He glances at the chat and sees Alpha5's name. Even if he doesn't know what he said, it's enough to know that he's watching. 

"Fuck, fuck," Stiles gasps out again. "I'm gonna come, I'm gonna...ah!" 

Stiles' hole clenches down around his fingers as he comes, his little cock spurting weakly over his stomach. Stiles keeps his fingers in himself for a few moments, luxuriating in the feeling of being so full. With a regretful sigh, he pulls his hand free and wipes it on the towel he has nearby. He smiles sheepishly at the camera and pulls the laptop closer to check the group chat. 

"I'm glad you like it," Stiles says in answer to their approval.

_HungDude255241: fuk you're sexy. I'd luv to pound that virgin ass_

_Bob23: Such a good show, littlered_

_TheTrinity: Love your itty bitty dick_

Stiles chats naked with the group for a while. Some make him want to roll his eyes, but he tries to respond to everyone. Some, like Alpha5, make him wish he had a better refractory period, because damn. 

_Alpha5: You look so beautiful when you cum, your cute little cocklet jerking with pleasure. I'd love to get my mouth on you, coax you into orgasm after orgasm._

It should be cheesy, like HungDude255241, but for some reason, Alpha5's words always make heat gather in his belly. 

_littlered: You wouldn't mind playing with a virgin?_

So he's baiting them, so what? He knows it's part of his appeal, and if it works them up and gets them to tip him more, he'll be shameless.

_Alpha5: It would be my genuine pleasure to explore you and show you the wonders that can be pulled from your delicious body._

_HungDude255241: Hel lyeah I'd fuk a virgin! They're always super tight!_

_Bob23: Not at problem at all! It'd be hot._

But it's really Alpha5's responses he looks for.

He stays up later chatting with the group (mostly Alpha5, let's be honest) than he'd intended and almost oversleeps the next morning. He manages to get out of bed and take a quick shower in time to get to class. He only has to run a little bit. He still gets his usual seat next to Erica, though that's probably because she glares at anyone but Stiles that tries to sit next to her.

"Cutting it a little close," Erica says.

A second later, the professor walks it and Erica turns her attention away from Stiles. She's surprisingly strict about not talking in class when she's not supposed to. Stiles thinks it's because she's the first in her family to go to college and she wants to make it count, but he isn't sure. Whatever the reason is, he can't talk to her until their English class is over and they make their way across the quad for lunch.

"Why so late?" Erica asks as they buy their food.

"I got caught up in the chat last night after my show," Stiles says.

"You mean you got caught up with Alpha5," Erica says knowingly. "Still harboring that crush, then?"

"It's not a crush!" Stiles protests. "I've never met the guy! We don't talk outside of a chat box on a cam website. That's not the basis for the crush."

"And yet here you are, almost late to class because of him," Erica says.

They walk deeper into the student union, finding a small table free by the window.

"I was not," Stiles says, but he knows this is getting perilously close to a case of doth protest too much. 

"Uh huh," Erica says, taking a bite into her sandwich. "I don't know why you stay around to chat with them anyway. I'm thinking about disabling mine, it's just full of too many creeps and pervs."

"You're on a webcam model site," Stiles reminds her. "We don't really have room to throw stones."

"I will absolutely throw stones at the ones that get creepy," Erica says. "Sexual, I don't mind. But I have boundaries. I'm performing a service, not asking for creeps to smell my underwear and I'd like it if they'd stop asking."

"...I don't have an answer to that," Stiles says.

"I thought you might not," Erica says. 

Stiles doesn't blame her for disabling the chat feature on her site. He does get a few gross people every once in a while, but he's seen some of the shit Erica gets and has to admit, she has it a lot worse when it comes to that. 

"I just talk to them because some of them are funny. Sometimes they do suggestions for next videos that I wouldn't have thought of. A few even buy things off my Amazon wishlist if they're feeling like tipping in gifts," Stiles says.

"Well, good," Erica says. "I should attach mine, I do have some generous tippers...Hmm."

"Come on," Stiles says, balling up his trash. "We're going to be late to our next classes."

Stiles tries to do two shows a week, but then midterms happen and he just doesn't have time. He logs on briefly to send a message out apologizing, but doesn't stay long enough to talk to anyone before going back to work. His midterm for his English class is a polished portfolio of all the work he's done so far this semester, which is such a major pain in the ass. He's trying to study for his biology test and history at the same time as editing his portfolio and Jesus H. Christ, it's like his professors all hate him. His two tests are even on the same day.

Despite struggling to find the time to study around his job's schedule, Stiles thinks he manages to do okay on his tests. He's glad he remembered to put his phone on vibrate before his bio test because someone keeps calling him throughout his test. It's a bit distracting and he has to go back and change a few answers that he got wrong because his focus was split between that and the buzzing in his pocket. 

He turns his test in and heads out into the crisp spring air. His phone vibrates again and he closes his eyes in frustration before pulling it out of his pocket. It's Deputy Parrish and Stiles' insides go cold. There's only one reason he'd be calling him non-stop.

"What happened?" Stiles asks in lieu of hello.

 _"It's your dad,"_ Parrish says. _"There was a domestic dispute call and he was shot."_

It's like the world falls out from under Stiles' feet. He can tell that Parrish is talking, but he can't really hear what he's saying for a few moments. 

"My dad," Stiles manages to say. "Is he okay? Is he...he's not...?"

 _"He's in surgery now,"_ Parrish says. _"It looks like he's going to be okay. It was in the shoulder and the bullet shattered, so they have to get all the fragments out."_

"Okay, okay," Stiles says, taking deep breaths. "Okay, so I just finished midterms. I'm going to run home, pack a bag, and get on the road. I should be there by 7:00. Where is he, Beacon Memorial?"

 _"Yeah,"_ Parrish says. _"Look, don't rush. He's going to be in surgery for a while and the last thing he needs is you wrapping yourself around a tree because you're driving like a maniac to get here."_

"He's my dad, Parrish," Stiles snaps. "I'll drive like a maniac if I want to."

Parrish sighs, but seems to know better than to fight. 

_"Call when you're here, I'll come down and meet you,"_ he says. _"Drive safe."_

"Bye," Stiles says.

Stiles dashes to his car, texting Erica along the way to let him know that he won't be in classes for a bit. He'll have to email his professors, see if they can work something out with him. It takes him less than ten minutes to throw some clean clothes and his laptop into his bag and get out the dorm door again. He's lucky enough not to have a roommate so at least he doesn't have to deal with that. 

The drive to Beacon Hills seems to take forever, even though Stiles is going a straight 80 MPH the whole time. It's a miracle he doesn't get pulled over in all honesty. He barely remembers the drive. He calls Parrish as soon as he gets into the hospital. Parrish tells him his dad is still in surgery and they're on the fourth floor. 

Stiles can't wait for the elevator, even though he knows it's probably faster than running up the stairs. He takes the stairs anyway, at least he's moving. It seems like half the department is in the waiting room when Stiles gets in and as much as he appreciates the thought, he wishes they would all go away. He doesn't want their looks of pity or worry. Yeah, their boss is in there, but it's Stiles' _dad_. Parrish, god bless him, seems to notice this and quietly ushers people away from him, letting Stiles talk to the man at the front desk.

"My dad is Sheriff Stilinski," Stiles says, out of breath from running up the stairs. "He was shot, he's in surgery, can you tell me anything?"

"All I know is he's still in surgery, I'll let you know when I know something more," the receptionist says. 

Stiles wants to scream at him, wants to yell that that isn't good enough, but he just says, "Okay," and walks back to the waiting room, collapsing into one of the hard hospital chairs. Parrish comes to sit by him, but doesn't try to talk or console him, so Stiles allows it.

They sit there in silence for what feels like hours, Stiles isn't sure, he forgot to check the clock. Stiles looks up every time he hears a door open, but no one comes over to them. Eventually, deputies start to trickle out as calls come in and they can't put it off any longer. By the time the surgeon comes out, it's just Stiles and Parrish.

"Mr. Stilinski?" the surgeon asks.

"Me," Stiles says, hopping up. "How's my dad, is he okay?"

"He's going to be just fine," she says and Stiles almost collapses sideways into Parrish. "It's going to take some time to heal and he'll need some physical therapy if he's going to retain full movement of the arm."

"Okay, but he's fine, right? I can see him?" Stiles asks.

"You can see him," she says. "He's in room 406. He won't be awake for a bit, but you're welcome to sit in with him."

Stiles barely waits for her to stop speaking before he's off down the hall, searching for his dad's room. A nurse is finishing up and lets him in, reiterating that it'll be a bit before his dad is conscious. Stiles doesn't care, just collapses into the chair next to his dad's bed. Stiles tries to stay awake, he wants to be here when his dad wakes up, but he finds himself drifting off, the stress from the day finally catching up to him. He tries to fight it, but he ends up nodding off, his head resting on his dad's bed.

Stiles wakes up to soft voices. At first he thinks he left the TV on and is a bit confused, before the hospital sounds register. Stiles bolts upright in his chair to see Parrish and his dad talking quietly.

"Why didn't you wake me up?" Stiles snaps.

"I told him to let you sleep," the sheriff says, sounding tired.

"How are you feeling? Stupid question, you feel like you got shot," Stiles says, hovering over his dad. "Do you need anything? Are you, fuck, are you _okay_?"

"I got shot in the shoulder, I'm not _okay_ ," the sheriff says, but he's smirking a bit when he says it. "Stiles, I'm going to be fine. The paid meds they have me on are good. You'll be able to go back to school soon."

"Like hell," Stiles says. "I'm staying. You're going to need help."

"I think I can manage by myself," the sheriff says.

"Well that's lovely for you, but I'm pretty sure the doctor will disagree," Stiles says.

To the sheriff's dismay, his surgeon agrees with Stiles, suggesting someone help with him with bandage changing and anything that requires undue use of his arm for at least a few weeks. The sheriff argues with Stiles, and Parrish offers to help, but he falls quiet under the ferocity of Stiles' glare. 

"I already emailed my professors and we're working it out," Stiles says. "They're letting me do homework online as long as I'm back within four weeks."

"I don't know if I can handle four weeks of your mothering," the sheriff says jokingly, but Stiles is pretty sure there's a grain of truth behind those words. 

The weeks ooze by slowly. It's a mess of changing bandages, taking his dad to doctor's appointments, making sure he doesn't irritate his stitches, cooking, cleaning, doing everything his dad might require two arms for. The sheriff is itching to get back to work but the deputies have staged a mini mutiny and refuse to let him back in the station until he's cleared to work. After two weeks, they do let him look over cases from his house, though. 

Stiles doesn't have time to log back into his cam site and even if he did, he's not comfortable doing a show when his dad is one thin wall away. When he's not taking care of his dad, he's trying to make sure he's caught up on all the work he's missing. He and Erica share English, so he gets notes from her, and manages to finagle notes from kids in his bio and history courses, but they're not the same as his own notes and it takes him a while to slog through them. 

Finally, a few days before Stiles needs to go back to Berkeley or risk getting a failing grade in his classes, his dad is cleared for work.

" _Light_ work," the doctor reminds him. "No lifting, no driving. You're on desk duty, Sheriff Stilinski."

Stiles hugs his dad for a long time when he leaves, mindful of the hurt shoulder. 

"Just - call if you need anything, okay?"

"I'll be fine, Stiles. Parrish and Tara are taking turns shuttling me around. I have managed to live my life without you, you know," the sheriff says. 

"Yeah, yeah," Stiles says, but he can't stop his worry.

As soon as he gets back to the dorm, he texts both his dad and Erica to let them know he's back. Erica sends back a dozen exclamation points and demands that they do lunch the next day. Stiles sends back an affirmative and before he can think of anything else, falls asleep on his narrow bed.

The next week is a haze of classes. He has tests to catch up on, essays to make sure are complete, but finally, he feels like he's in a good place. He's lucky his teachers were so accommodating, but he figures no one wants to be the guy that messes with a cop's kid. Best of all, he has time to log back in to his cam site. He's not sure what he's expecting, but a bunch of angry comments were definitely on the list.

It seems that everyone has a complaint. Where is he? Why isn't there any new content? Why didn't he tell them he was taking a break? Some get downright rude, calling him selfish and a whore. Stiles almost blocks those people because honestly, he just doesn't have it in him to deal with them, but his dad's medical bills are piling up and Stiles no longer is doing this just for fun, he actually needs to money now. His dad doesn't want him to help, doesn't want him to know the cost of being shot, but Stiles had made a copy of one of bills so he has the account number and everything he needs to make payments.

Stiles pulls up the group chat and sends out a message to whoever is online.

_littlered: Hey, everyone. Sorry for the long delay. My dad was hurt at work and I've been taking care of him. I'm back now though! I'll be starting up twice weekly shows again starting tomorrow._

Stiles gets responses immediately, everything from 'welcome back' to 'it's about time!' Stiles rolls his eyes at someone's request for him to do a show right that minute and tells them that nah, he's going back to his Saturday and Tuesday night schedule. He talks for a bit longer and is about to log off when he gets a ping that someone sent him a private message. Usually he deletes those, as per his policy, but this one is from Alpha5 and he's curious.

_Alpha5: I'm sorry to hear about your father. Are you all right?_

Stiles stares at the message for a moment. Honestly, it's not what he'd expected. Maybe a request for a private show, as some subscribers have done? But not this, not treating him like he's an actual person.

_littlered: I appreciate that. I'm okay, it was just stressful. I was a little shaken up, you know?_

_Alpha5: I can imagine. Do you want to talk about what happened?_

Stiles does, he realizes. He's talked to Scott and Erica about it briefly, but he's been so busy that he hasn't really had a chance to sit and digest everything that's happened, to really discuss it. The thing is, Stiles knows his rules on online privacy, so he has to be careful about what exactly he says.

_littlered: My dad was shot. He's a cop. It was in the shoulder, so he made it, but he's going to have a lot of physical therapy to make sure his arm retains movement._

_Alpha5: I'm so sorry. That's something no one should ever have to go through. Do they have the person who did it?"_

_littlered: Yeah, he's in jail. My dad's on desk duty for the foreseeable future, which he hates but he needs, you know? He's fighting the doctors every step of the way, trying to push boundaries and do more than he should._

_Alpha5: I'm not a doctor, but it seems like following doctor's orders is the only thing that's going to help him here._

_littlered: YEAH! Thank you! He keeps insisting he can handle more and trying to drive himself places. He just can't admit that he's limited right now._

_Alpha5: It must be tough to go from being a perfectly capable adult to being dependent on others. Still, I hope you manage to knock some sense into him._

_littlered: I do what I can. I guilt him with the whole 'if you're not going to do it for yourself, at least do it for me' thing, but I don't know how much longer that'll work._

_Alpha5: Milk it for all it's worth until then._

_littlered: lol that's the plan. Thanks, man, I needed to vent about it._

_Alpha5: Any time. I'm glad you're back, and not just for your tantalizing performances._

_littlered: Well I'll be back to sessions tomorrow, so you'll get plenty more_

_Alpha5: I look forward to it. I'm glad everything is (mostly) okay and you're safe. You had me worried._

Stiles can't fight his grin at that. He's glad Erica isn't here to tease him about his ridiculous crush.

_littlered: Thanks, man, I appreciate it. But so far, all's quiet on the western front, and let's hope it stays that way._

_Alpha5: I hope that for you as well. I'll see you tomorrow, little one._

_littlered: See you. Thanks again._

_Alpha5: You're welcome._

-

It's Alpha5 that Stiles is thinking of as he turns on the camera for his next session. It's Alpha5, who is just a faceless man to him (his user photo is a shot of a thick neck and deep v-neck, cutting off his face), that Stiles thinks of as he strips to nothing, then opens his thighs to show off the plug buried deep in his ass. It's Alpha5 that Stiles thinks of as he straddles a pillow, grinding against it as he moans and hisses.

Stiles doesn't touch his tiny cock, letting it bounce as he humps the pillow, chasing the pleasure he gets whenever the toy presses against his prostate. He moans loudly, not even having to fake it because fuck, why didn't he think to do this before? He's seen girls humping pillows and wondered what they could get out of it, but this feels fantastic.

Stiles almost moans out 'Alpha' as he comes, but manages to keep it to a wordless moan. He's so oversensitive with the plug, but Stiles doesn't want to be empty, so he settles onto his bed to chat with the viewers with the plug still buried inside him.

_HungDude255241: Didn't take the plug out? lil slut_

_Bob23: Awesome, littlered. Love watching you_

_WowCocks: So sexy_

_littlered: Thanks everyone! It really gets me going knowing you're all watching_

He's not lying. Knowing that he's being desired, that people are watching him and getting off on him urges him on. A private message pops up from Alpha5 and Stiles can't help but grin.

_Alpha5: That was quite the show. Have you ever done that before?_

_littlered: I've played with the plug, but never with the pillow before._

_Alpha5: You looked wonderful, especially the beautiful flush spreading down your body as you got closer and closer to coming._

_littlered: Well, I'm blushing now_

_Alpha5: I can see that. You look beautiful like that, I can only imagine how perfect you would look all fucked out beneath me._

Stiles' cock makes a valiant effort to get hard at that, but he's just too spent.

_littlered: Careful, I could get a big ego_

_Alpha5: You would deserve it._

Stiles grins stupidly, and he's sure the people in the group chat think it's about what they're saying, but Alpha5 just knows how to push Stiles' buttons apparently.

After that session, Stiles and Alpha5 start talking on the site more frequently. Stiles gives updates on his dad's progress, shares his stresses over the hospital bills, and his worries over failing out of classes. He learns more about Alpha5 in response, too. The man is a CEO of some company, though he won't say what (not that Stiles blames him), he has a big family that likes to pry, and a sphinx cat named Felicia. 

Stiles is chatting with him after a show when he gets the alert that someone has tipped him. This happens sometimes, especially if someone really enjoyed the show (tips were astronomical the first time he played with his ass), but it's been happening a lot more lately, and a lot of it is Alpha5. The man was a good tipper in general, but lately he's tipping close to double.

_littlered: You don't have to do that, you know._

_Alpha5: I have no idea what you're talking about._

_littlered: Uh huh, sure_

_Alpha5: If I did, hypothetically, I would tell you that tipping is a normal part of a service. And, hypothetically, that you're going through your savings on your father's hospital bills and that I, hypothetically, make more than enough to contribute._

_littlered: I, hypothetically, would remind you that you already pay for access to videos._

_Alpha5: I, hypothetically, would know that._

Stiles shakes his head, but he's smiling. Far be it from him to dissuade someone from tipping him after he jacks off on camera.

_littlered: Well, thank you._

_Alpha5: You're welcome. I do have a question about the Amazon wishlist you have._

_littlered: Hit me with it_

_Alpha5: If someone were to purchase something off of it, would you use is on camera?_

_littlered: That depends on what it is, but mostly likely yes._

_Alpha5: The clear fleshlight?_

Stiles' gut clenches in anticipation. He's always wanted to try a fleshlight. It's basically a tube with soft, flesh-like material inside. They have opening that are shaped and colored like porn stars' vaginas, but he has his eye on the clear one that has the opening of an ass instead of a pussy. And it's clear so he can see his cock sliding in it.

_littlered: Absolutely. I've been wanting to try that for so long, I can't even tell you._

_Alpha5: I very much love the idea of watching your tiny little nub disappear into that, see how far it can reach._

_littlered: Fuck. Yes, definitely that._

_Alpha5: Done. Hopefully it comes by the next session._

It does, and Stiles is ecstatic. He's nearly bouncing in anticipation before the next show. He strips quickly, not bothering to be sensual. There's some amusement on the group chat at how excited he seems.

"Sorry, guys," Stiles says with a blush when he realizes he's already naked. "I'm just really excited because one wonderful person bought me this from my Amazon list, and I've been dying to try it." Stiles holds up the clear fleshlight with a grin. "I haven't used it yet, I wanted you guys to see it for the first time."

Stiles lubes up his little cock and with no further ado, presses into the fleshlight. It's strange, but it feels so, so good. He's never fucked anyone, but he can't help but think that this is realistic as hell. The soft material clings to his cock, swallowing him up. Stiles groans and looks down, seeing through the clear material how his cock only manages to get a couple of inches inside, seeing all the extra space that could be taken up by someone more well-endowed. 

"See how much room is left?" Stiles asks breathlessly. "I can barely get two inches inside, and there's like eight more inches left. Someone with a bigger cock could fill this all but, and I can barely get inside."

_Alpha5: You little dicklet is so cute in there, can you even feel anything?_

Stiles moans at that and fucks into the fleshlight, loving the drag of the soft material against his dick. Alpha5 keeps spurning him on, telling him how wonderful he looks, commenting on how small and useless his cock looks inside such a big toy. Stiles whines at each comment, hips erratically thrusting forward and he jacks himself with the fleshlight. He's getting close, Alpha5's words making it harder for him to hold back. With a loud moan, he comes inside the toy, his little cock jerking, come spurting out of him.

Stiles pulls out with a hiss at the sensitivity, setting it aside to clean later. He goes back to the chat to see that some people weren't a fan, oh well, but the majority of them loved it and can't wait to have it uploaded to the site so they can watch it again.

Stiles opens up the message with Alpha5, as he usually does now, and his heart stops for a second.

_Alpha5: I wouldn't upload that video to your archive if I were you. I can see the Berkeley flag on your nightstand and I'm sure that's not information you want getting out._

Stiles whips his head around and sure enough, there's the little flag that says Berkeley on it. They'd been given out to all students as some kind of school spirit week and Stiles had tossed it onto his nightstand before promptly forgetting about it.

"Shit," Stiles says. "Shit, fuck."

Stiles opens the group chat.

_littlered: the site ate that video, guys. It won't let me upload it :( if there's interest, I'll do another fleshlight one and upload it next time._

There's the outcry of agitation at that, annoyance that the site would do such a dastardly thing and enough people are interested that Stiles promises to do another fleshlight session next time. Alpha5 is strangely silent. Stiles takes a few deep breaths, then opens the window with Alpha5's chat.

_littlered: Thanks. I hope no one else noticed but you. And I'm pretty sure you aren't a stalker, so, good?_

_Alpha5: Not a stalker, no. I do happen to live nearby though. Would you want to get a cup of coffee?_

Stiles' brain screeches to a halt. On the one hand, everything he knows about internet safety is saying that NO this is a godawful idea. A voice that sounds a lot like Erica is screaming at him that he's an idiot. On the other hand, fuck, he really likes Alpha5, okay? And he's curious. Stiles bites his lip, his fingers hovering over the keyboard, when he receives another message.

_Alpha5: It's fine if not. I won't be offended. A strange man from the internet wanting to meet you I'm sure raises some red flags._

_littlered: A few, yeah. I mean, you've seen all of me and I don't even know what you look like._

Less than a minute later, a link appears.

_Alpha5: That's me._

Wary, Stiles clicks on the link. It's a selfie of a man holding a piece of paper with today's date on it to prove it's not a stock photo and _damn_ , he's gorgeous. He has bright blue eyes and artful stubble and a thick neck that Stiles recognizes from his user photo, and immediately wants to bite.

_littlered: I'm glad you put up the sign holding today's date or I absolutely would have thought you were a model, what the fuck_

Okay, so it's not the most elegant thing Stiles has ever said, but whatever, his crush on Alpha5 just grew times a million.

_Alpha5: Haha no, not a model. Thank you, though._

_littlered: Are you sure? Because dude..._

_Alpha5: Flattery will get you everywhere. Now that you know I'm not nintey years old, are you open to coffee?_

_littlered: I was interested before, just so you know, but yeah, I am. Let's do it._

_Alpha5: Perfect. I'll let you pick where and when so you're as comfortable as possible._

_littlered: Luring me into a false sense of security, smart._

_Alpha5: I aim to please._

Stiles and Alpha5 set up a time and place for the next day before Stiles has to go and work on his essay, but he'd finding it hard to focus on history when his mind just wants to linger on Alpha5.

The next day in class, it's almost impossible for Stiles to pay attention. Erica keeps shooting him odd looks but he just shrugs. It's not until it's after class and they're eating at one of the picnic tables in the quad that Erica pounces. 

"Spill," she says.

"Where?" Stiles asks, looking down at his shirt. He'd been so careful with the barbeque sauce, too...

"No, spill the beans," Erica says impatiently. "Why are you so weird today."

"Oh," Stiles says. "Uh, you remember Alpha5?"

"How could I forget?" Erica asks with a leer and a wink.

"Well, he and I are kind of getting coffee today."

"WHAT?" Erica shouts. People around them look up in alarm but she doesn't pay them any attention. "Have you ever watched Dateline? You can't go!"

"Erica - "

"He could be old and saggy! He could be a serial killer! He could be - "

"So hot," Stiles moans, pulling out his phone and showing her the picture he'd been sent last night.

"That's not - oh my god, I would sit on his face," Erica says.

"Right?" Stiles asks.

"Still! Hot men can be serial killers!" Erica says.

"That's why I'm showing you what he looks like and telling you where I'll be, just in case something happens," Stiles says.

"This is a colossally bad idea," Erica says.

"Probably," Stiles says. "But I'm doing it anyway."

"Ugh, fine! Text me every half hour or I come in screaming," Erica demands.

"You got it."

Stiles is nervous about being late, so he gets to the coffee shop fifteen minutes early, only to see that Alpha5 is already there. He's sitting at a table in the corner, completely engrossed in the book he's reading. Stiles smiles slightly and puts in his order before walking over. He clears his throat lightly and smirks when Alpha5 startles, looking up at him in annoyance that quickly melts away once he sees who it is.

"Alpha5, I presume?" Stiles asks, holding out his hand.

"Littlered," he says. Instead of shaking Stiles' hand, Alpha5 takes it and brushes a kiss over his knuckles. 

"Stiles," Stiles says. "I'm Stiles."

"Peter," Alpha5, Peter, says. "It's a pleasure to meet you."

"You too. Wow, I'm glare you're real," Stiles says, sliding into the set across from Peter. "I mean judging from your picture, I figured you were, but you're also really fucking hot and maybe you're good at photoshop, who knows? Anyway, my friend owes me $20."

Peter, instead of looking put out by the rambling, just looks amused.

"You bet that I wouldn't be ugly?" Peter asks.

"She thought you weren't real," Stiles says. "Or maybe a murderer, which remains to be seen."

"Well I'll do my very best to convince you I'm not a murderer," Peter says.

Stiles is worried conversation will be awkward. What do you even say to a guy that pays to watch you masturbate? But conversation just flows organically, and not because of Stiles just blurting out whatever comes to mind. Peter's smart, Peter's charming, and Stiles' crush is so, so growing. They talk about everything from Stiles' classes to Peter's job to reading Google reviews of churches for fun.

"When we're bored, that's what Erica and I do," Stiles explains after he texts Erica for the third time that he's still alive and Peter isn't a serial killer. "We look up churches and read their Google reviews. This one church in Georgia had this really angry lady named Debbie call out Pastor Dave for sleeping with parishioners."

Peter laughs. "Sounds like Debbie was jealous," Peter says.

"Of horndog Pastor Dave? Doubtful," Stiles says. 

When they're outside the shop, about to go their separate ways, Peter cups Stiles' jaw in his large hand, running his thumb over Stiles' cheek. Stiles' breath catches as he stares into Peter's clear, blue eyes.

"Can I see you again?" Peter asks softly.

"Yeah," Stiles says. He doesn't even think about it, he wants to see Peter again desperately. 

Peter smiles and leans in slowly, pressing a soft kiss to Stiles' lips. Stiles hums into the kiss, pressing closer to Peter. He's only kissed a handful of people before, but even he can tell that Peter knows what he's doing. Peter gently coaxes him to deepen the kiss, licking into Stiles' mouth and making him moan. Stiles is clutching at Peter's arms when he pulls back and Stiles is gratified to see that he's slightly out of breath.

"As much as I would love to continue this, darling, I don't think you want to put on a show for the people inside," Peter says.

Stiles blushes, remembering they're right in front of the coffee shop window. He refuses to turn and see how many people are watching them.

"Yeah, probably not," Stiles says. He pulls out his phone and hands it to Peter. "Here, put your number in. I'd rather talk to you this way than just online."

Peter puts his number in and hands the phone back. He gives Stiles one last fleeting kiss before they part. Stiles' lips tingle the whole way home.

-

The great thing about dating Peter is...well, everything. Peter's hilarious, and sweet, and funny, and a complete sarcastic asshole. Stiles loves it. He feels like Peter matches him well, matches his own brand of dickishness. Then there are times when Peter calls him just to hear his voice before bed and Stiles feels like melting into the floor.

One of the things Peter insists on is always paying. Stiles doesn't know if it's just how he is, or if he's very conscious that Stiles rapidly went through his savings helping pay his dad's medical bills, but whatever it is, he pays.

"Peter, I can afford it, I don't want you spending your money on me," Stiles says.

"What if I want to?" Peter says.

"You already do!" Stiles says. "Twice a week! Even though I told you you don't have to."

"And I do so of my own free will, no one is forcing me," Peter says. "Just accept the popcorn, Stiles."

Erica meets Peter a few weeks into Stiles and Peter dating. Stiles tries to put it off for as long as possible, but Erica flat out refuses to leave one day when she knows Peter is picking Stiles up. She waits patiently and follows Stiles out to the parking lot where Peter is just pulling up. Stiles kisses Peter hello then waves a helpless hand at Erica.

"This is my friend Erica," Stiles says. "She's nosy and insisted on meeting you."

"It's a pleasure," Peter says, shaking Erica's hand. 

Erica's eyes narrows and her long nails dig into Peter's hand.

"If anything bad happens to him, anything at all, I will break every bone in your body and bury you alive," Erica hisses. "His dad's a sheriff, I'll get away with it."

"Erica," Stiles hisses. 

"I won't ever let anything bad happen to him," Peter says solemnly. "I care about him too much."

Stiles wants to coo at asshole Peter displaying his emotions, but he figures now isn't the time. Erica nods and pulls her hand back, leaving crescent moon-shaped indents in Peter's skin. Stiles apologizes all night for Erica, but Peter tells him it's fine, that he isn't surprised at some level of animosity considering how they met. Which yeah, Stiles can understand. He's pretty sure a meet-the-parents/friends type of moment isn't going to go well when they have to explain that Peter frequents a cam site where Stiles performs as a small-cocked virgin. 

"You really don't care that I'm a virgin?" Stiles asks when they're back in his room after their date. Peter's kissing his way down Stiles' neck, his hands tight on his waist.

"Not at all," Peter murmurs against his skin. "If and when you decide to have penetrative sex, and if it's with me, I'll be glad to divest you of that pesky virginity."

Stiles laughs, which turns into a moan as Peter bites at his neck. "Only you would use divest when you're a second away from putting your hand in my pants."

Peter chuckles, but doesn't contradict him. He flicks open Stiles' jeans, dipping his hand inside to palm at Stiles' little cock. It easily fits in his hand, making Stiles blush, but Peter always seems to love it, can never seen to get enough of watching Stiles' dick disappear into his hand. 

Stiles whines and buries his face in Peter's neck and Peter jacks off his tiny dick, always so close to coming from Peter's expert hands. Peter laughs softly in his ear, his free hand tight on Stiles' waist.

"So good for me, Stiles," Peter murmurs. "Such a good boy for me. Are you going to come for me? Come in your pants like a teenager from having your little cocklet played with?"

Stiles whines and presses into Peter's hand, desperate for more. Peter tightens his hand and moves it fast, giving Stiles the stimulation he desperately needs. 

"This is barely even a cock," Peter says, mouthing at Stiles' neck. "It's more of an oversized clit." 

It's true. When Stiles looks down, he can't even see his dick in Peter's hands. It almost looks like Peter really is playing with a clit. Stiles groans, body shaking under Peter's talented hands and mouth. 

"I'm gonna come, Peter," Stiles whines, shaking in Peter's arms. "Please, please..."

"Go ahead, come for me, Stiles," Peter says, tightening his hand even more. 

Stiles spills over Peter's hand with a sigh, his body feeling limp and full of pleasure. He paws at Peter's pants until with a laugh, Peter undoes his jeans. Stiles drops to his knees instantly and licks up Peter's thick cock. He's the exact opposite of Stiles, thick enough that Stiles' fingers barely can wrap around him and long enough to choke Stiles every time. Stiles loves it, loves the difference when they line their cocks up next to each other.

Stiles sucks Peter down, licking and working at Peter's dick until the man is wrapping a hand in Stiles' hair, all but fucking his face. Stiles moans, taking as much of Peter into his throat as he can. Peter hisses and pulls at Stiles' hair, his only warning before Peter is coming down his throat with a growl. He yanks Stiles up at kisses him roughly, never shy about kissing him after he gives head. Stiles loves that about him. Peter steers them to the bed and they spend a long time sharing heated kisses that turn lazy and sleepy, until Stiles eventually falls asleep wrapped in Peter's arms.

Another great thing about Peter? Peter doesn't demand that he give up being a camboy. Even better, he gets off on it, on everyone wanting what he has. Sometimes he comes to Stiles' sessions to sit just outside of the camera's reach and watch him perform. Peter will rub his hard cock through his pants, pulling out his erection while Stiles is bare in front of the camera, riding a toy or stroking himself or playing with his hole. When he's done, Peter will throw him down on the bed and swallow him down, or finger his hole, press against Stiles' prostate until he's coming again with a shout. He's sure his neighbors hate him.

There's a week between the end of Stiles' classes and the beginning of summer session. As much as Stiles would love to spend it in bed with Peter, he has to go back and visit his dad. Surprisingly, his dad's actually been taking the doctor's and physical therapist's advice (Stiles strongly suspects Melissa's influence) and is still taking it slow. He protests a bit, but lets Stiles help him around the house. 

Stiles has been gone for five days when he gets the idea. He makes sure his dad asleep in the room next door before he strips himself down and lies down on his bed. He pulls out his phone and Facetimes Peter, knowing that even though it's late, he'll still be up. 

_"Hello, Stiles,"_ Peter says when he answers. He's in bed, the dark blue pillowcase framing his face. He raises an eyebrow at Stiles being shirtless. _"Is there something I should know?"_

"Nothing," Stiles says innocently. "Just was thinking about you."

 _"Oh?"_ Peter asks.

"Mmhmm," Stiles says, reaching a hand between his legs. His little cock is rapidly hardening and he squeezes it gently, gasping.

 _"Show me what you're doing, little one,"_ Peter says. 

Stiles switches to the forward facing camera and angles it down so Peter can see his hand moving on his small dick. Peter groans and there's the rustling sound as Peter settles his hand in his pants.

 _"Thinking of me makes you play with your cute little cock, does it?"_ Peter purrs.

"Yeah," Stiles gasps. He rubs over his cock, precome slicking the way. "I was th-thinking, I want you to fuck me."

 _"Oh?"_ Peter asks. Stiles can tell his playing with himself on the other end of the phone. 

"On camera," Stiles says. Peter groans, head thrown back. "I want you to fuck me for the first time on camera, I want everyone to watch me lose my virginity to you."

 _"God, yes, sweetheart,"_ Peter says. The camera is shaking slightly and there's the slick, skin-on-skin sound as Peter jacks his thick cock. _"I want them all to see me fuck you open, get that pretty hole loose and wet, your pathetic little nub dripping for me."_

"Yes, Peter," Stiles whines, rubbing at his cock. He's close, his dick twitching in his hand. "I'm close."

 _"Me too,"_ Peter admits. 

The camera is shaking more forcefully as Peter fucks his fist. Peter groans and stills, eyes closed in bliss and that pushes Stiles over the edge, that thinking about taking Stiles' virginity makes Peter come. Stiles comes over his fist, his cock dribbling white. 

"So," Stiles says breathlessly, switching the camera to front facing so Peter can see his face. "When I get back?"

 _"Yes, sweetheart. When you get back,"_ Peter says. He still sounds breathless and Stiles takes great pride in that.

-

"Hey guys," Stiles says cheerily, waving into the webcam. Peter is seated next to him, his hand resting on Stiles' thigh. "As you can see, I have a friend here with me. This is my boyfriend and he and I have decided to have sex. On camera. You get to see him take my virginity, fuck me in the ass for the first time."

The group chat positively explodes. Some are insanely jealous, asking who the hell this guy is, others are excited, hungry for seeing littlered get fucked.

"So, yeah, without further ado, mph!" 

Stiles turns back to Peter just in time to get kissed hard and pushed down onto his back. Peter strips him quickly, like he doesn't see Stiles bare all the time. 

"You look so good like this, all bare and beautiful," Peter says, undressing himself while staring at Stiles. 

"Pe - Alpha," Stiles whines, forgetting for a moment that they're using their usernames. He can see the chat light up with demands, asking if this is Alpha5. "Yeah," Stiles answers them. "This is Alpha5."

Messages rapidly appear in the chat window but Stiles ignores them, choosing to watch Peter crawl up his body before sucking Stiles' cock into his mouth. It's easy for him to get the two-and-a-half inches into his mouth, easy for him to suckle and lick Stiles' cock until he's close to orgasm. Peter stops in time, making Stiles whimper.

"Not yet, little one," Peter purrs. "Not until I'm inside you."

Peter takes his time opening Stiles up, wanting to make sure that his thick cock doesn't hurt Stiles. They've done this before, Peter fingering Stiles open and playing with the abused hole, but this is different. This has the intent with it and Stiles knows that soon, he won't be a virgin anymore. Peter's going to fuck him in front of all his viewers and knowing Peter, it's going to be amazing.

Peter's up to four fingers and Stiles feels like he's going to fly apart with need. He's never wanted something to be inside him so badly. He cants his hips up, trying to get more of Peter's thick fingers into him. Peter chuckles and purposefully brushes his prostate. Stiles mewls and clenches down on Peter's fingers.

Stiles whines at the loss when Peter pulls his fingers out, but soon enough, he's lining up his cock at Stiles' entrance. Stiles doesn't realize he's holding his breath until Peter tells him to breathe and bear down. Stiles gasps as Peter presses into him. This is nothing like the toys his has. Nothing has prepared him for Peter's girth, for the heavy weight of a real cock inside him. It doesn't hurt, he's too well-prepped, but it's a stretch.

"Pete - Alpha," Stiles says, breathless. 

"That's it, little one, let me take care of you," Peter says. His voice is tight, like he's trying hard not to fuck into him harder.

Peter starts slowly, easing in and out of Stiles with such great care, but Stiles wants more. He bucks his hips into Peter's thrusts, trying to get more of that thick cock into him. 

"Look at you," Peter coos at him. "You were made for this, made to get fucked."

"So good, it feels so good," Stiles whines. He isn't going to last long, not with the delicious way Peter's cock is dragging against his insides, not with how Peter reaches down and starts playing with his dick.

"Look at your tiny cocklet, my hand completely covers it," Peter says, rubbing his hand over Stiles' dick. Stiles blushes but his cock jerks in Peter's hand. "That's it, you love this, don't you? Love us staring at this small dick, at this useless little nub."

Stiles whines and bucks his hips at that. He's so close, and with Peter whispering filth in his ear, he can't hold back. He's going to spill his come all over himself, his pathetic little dick spurting white. 

"That's is, Stiles," Peter murmurs in his ear so the camera can't pick it up. "Come for me."

Stiles cries out when his orgasm hits him, coating Peter's hand in white and he jacks Stiles. His clenching hole just spurs Peter on. He grabs Stiles' hips and thrusts into him, chasing his own release. It's like the floodgates have opened and Peter can't stop telling Stiles how perfect he is, how much he loves his cute little cock and balls, how perfect he feels around him. He comes with a deep growl, stilling, his thick cock pulsing as he shoots deep inside of Stiles.

Peter collapses over him, burying his face in Stiles' throat. Stiles sighs happily, wrapping his arms around Peter. He'll pull the laptop to him in a few minutes and chat with the regulars, but right now, he's content. He's just lost his virginity, been fucked within an inch of his life by the sexiest man he's ever seen, he's more than happy to lie here in the afterglow.

Eventually, Peter softens enough that he slips out of Stiles. He kisses Stiles softly before rolling to the side, running his hand up and down Stiles' side. Stiles tugs the laptop closer and snorts a laugh. The chat is full of people either complaining that Stiles picked Alpha5 over them, or congratulating him on one of the hottest loss of virginity videos they've seen. 

"Thanks guys," Stiles says. "What would you think of Alpha joining me more on camera?" 

The answers are mixed, but the overwhelming majority wants to at least see Stiles fucked again.

"Don't worry," Peter purrs, slipping two fingers into Stiles' used hole, making him mewl. "He's going to get used again."

"See?" Stiles asks breathlessly. "We're good. Uh, talk to you guys later, bye." 

Stiles exits the chat and cries out as Peter fingers him until he's hard again, pulling another orgasm from him.

The video of him losing his virginity is the best seller he's ever had.


End file.
